Diisopropylethylamine → HCID 86685252, compound

HRID 522898Notes

Reaction equation

HRID 522898 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[F:20][C:21]1[CH:31]=[CH:30][C:24]([O:25][CH:26]2[CH2:29][NH:28][CH2:27]2)=[CH:23][CH:22]=1>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:28]2[CH2:29][CH:26]([O:25][C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:31][CH:30]=3)[CH2:27]2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochloride

Product 1

HCID 86685252HCID 86685252, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution 2,4-dichloro-5-fluoropyrimidine (150.0 mg, 0.898 mmol) in 2-propanol (4.00 mL) at RT was added N-ethyl-N-isopropylpropan-2-amine (0.469 mL, 2.70 mmol) followed by 3-(4-fluorophenoxy)azetidine hydrochloride (183 mg, 0.898 mmol). The resulting reaction mixture was stirred at RT for 1 h and concentrated. Purification of the crude using MPLC (25 g cartridge, 40 g column, 0 to 60% EtOAc-hexanes) gave 2-chloro-5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine (240.6 mg).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. customPurification of the crude

Sources & evidence

ORD record
ord-f552c45f9f0f4387923a90baebb6b905
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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